When Buddy Holly finally conceded to glasses, his vision was already 20-800. He had tried some of the earliest contact lenses. They became unbearable after about 10 minutes. So he got glasses. His first frames had thick plastic at the top, with a thinner, less obtrusive metal frame for the bottom half.

But his Texas optometrist, Dr. J. David Armistead, didn't see the point of going halfway with eyewear. While he was traveling in Mexico, he picked up two pairs of super-thick Faiosa brand frames, one black and one tortoiseshell. With some encouragement from Armistead, Holly chose the black ones. He came around to the idea that if he was going to wear glasses, he might as well wear some freaking glasses.

Tragically, Holly didn't sport the specs for long before the Beechcraft Bonanza transporting him, Richie Valens and The Big Bopper to a show crashed on The Day the Music Died in 1959. But in a relatively short time, the imposing frames became his trademark. They certainly didn't hinder his ascent to superstardom and heartthrob status. If anything, the specs added to his appeal.

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Holly was a harbinger of eyewear fashion to come, but an anomaly for his time. Until maybe a decade ago, four-eyed folks were largely stereotyped as intelligent but physically weak and awkward. Over time, though, our perception of smarties and their place in society has dramatically changed. As the presence of technology and tech culture increased in our lives, so did the profile of the intelligentsia. We love our tech gadgets not just for what they help us do, but also because we think they're cool. And the brainy people who built them are our heroes. Tech is cool, and smart people are cool. And smart people wear glasses.

At least that's how most of us see it: Studieshave shown that people wearing glasses are perceived as having higher intelligence as well as increased trustworthiness, reliability and diligence.

Mike Lee is co-founder of Mezzmer, an online eyewear company that mainly exists to keep geeks in $99 prescription frames. Says he: "People who are passionate and intelligent have become much more revered," says. And eyewear is an easy way emulate them. "Glasses are on your face so people see them immediately. They're a fantastic way to show your personality."

And while geeky frames have become more popular, they're not really part of a "pretty" aesthetic in the traditional sense. A study published in October found that people who wore rimless glasses were perceived as intelligent and trustworthy but also more attractive than those who wore more prominent frames. How was "More attractive" defined? As more "average" and "less distinctive." Which is the opposite of what people who go for bold frames are interested in. Thick eyeglasses might not be pretty like a rose but they are in your face—whether the lenses are prescription or not.

It's an approach to dressing fashion insiders know all about. They want to stand out, assert their personal style, not blend in. Jenna Lyons, creative director at J Crew and adored by the fashion set, is the quintessential example. Iris Apfel, an nonagenarian and much-loved figure in the fashion world wears hubcap-sized black rimmed-frames with lenses so thick they each look like little fish tanks (the older ladies have been doing this forever). Simon Doonan, creative ambassador at large for Barney's New York, placed statement-making glasses number one on his list of How To Become a Fashion Eccentric.

I own a pair of dark green Paul Smith frames that I love and get compliments on all the time, but as a woman who sometimes falls victim to the whole wanting to be appealing thing, I often shy away from wearing them. But I can tell you this: on my way to and from fashion shows, photographers have snapped "street style" photos of me pretty much only when I'm wearing them.

Geeks are the same way. They value at least appearing to be a person to reckon with over being inoffensively attractive. Yes, celebrities far and wide are wearing geeky glasses these days. But for them, the trend will pass, while actual geeks will continue wearing their Buddy Holly styles.

After the singer's glasses were thrown from the plane wreck, the hefty frames languished in an Iowa sheriff's office for 22 years before being recovered, still in one piece despite some nicks and scrapes. Holly's widow sold them in 1998 for $80,000.

Rimless glasses? Please. They never would have survived the crash.

Uniform is a weekly column exploring the relationship between geeks, fashion and fashionable geeks.